1. Leave isn’t just compliance—it’s career continuity, business continuity, and culture

Allison Whalen laid it out clearly: leave is a multi-dimensional challenge, and most companies only solve for one part of it.

"The first bucket is compliance. That’s obvious. But there’s also business continuity—how the work gets done—and career continuity—how the person comes back. And finally, what’s happening at home that affects how they show up."

Too many teams stop at pay and paperwork. If your culture fails people during or after leave, you lose trust—and often talent.

2. Managers can make or break the leave experience

Jessica Winder said it best:

"Policies mean nothing if managers don’t follow them. You can have the best intentions, but if the manager is pinging someone every week while they're out, it ruins trust."

She added that the return is just as critical:

"Ask them: what do you want back? Which projects? Set boundaries. They’re already coming back as a different person. They need clarity."

Train your managers. And hold them accountable.

3. Don’t sideline managers—empower them

Jennifer Henderson warned against one common trap:

"We’ve seen companies try to cut managers out of leave entirely to avoid risk. That never goes well. It sends the wrong message to the employee and isolates the manager."

Instead, give managers tools to recognize potential leave events and know what to say, what to avoid, and how to support without overstepping.

4. Sales comp plans for leave are broken—and you’re probably underpaying your top reps

Allison shared:

"I’ve never seen a perfect comp plan for leave. The worst is when someone hits 200% of quota while out, and only gets paid 80% of OTE. That’s how you lose your top performer."

Justin agreed:

"Treat them like a new rep when they return. Give them a ramp. Update quotas. It’s not just about fairness—it’s about retention."

Get proactive about ramp, pay, and expectations—before someone goes out.

5. Compassion is the strategy—and the ROI is real

Jennifer closed with a stat that says it all:

"Employees have a 10x assessment of their employer when a leave happens—either positively or negatively. That’s the moment that can make someone stay for a decade, or leave in six months."

Support doesn’t have to be expensive. A buddy walk-in, a clear plan, a follow-up message. The cost is low. The impact is huge.

Want to go deeper?

If you want to get into the nitty-gritty details and go even deeper than we did here, check out Tilt’s new guide on designing leave that actually works - it’s based on the insights from this episode.

See you next time!

P.S. If you like MPL, help us grow the show by giving us a 5 star rating on Apple or Spotify.